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Asymmetric, Remote C(sp 3 )-H Arylation via Sulfinyl-Smiles Rearrangement.
- Source :
-
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Apr 22; Vol. 63 (17), pp. e202319158. Date of Electronic Publication: 2024 Mar 20. - Publication Year :
- 2024
-
Abstract
- An efficient asymmetric remote arylation of C(sp <superscript>3</superscript> )-H bonds under photoredox conditions is described here. The reaction features the addition radicals to a double bond followed by a site-selective radical translocation (1,n-hydrogen atom transfer) as well as a stereocontrolled aryl migration via sulfinyl-Smiles rearrangement furnishing a wide range of chiral α-arylated amides with up to >99 : 1 er. Mechanistic studies indicate that the sulfinamide group governs the stereochemistry of the product with the aryl migration being the rate determining step preceded by a kinetically favored 1,n-HAT process.<br /> (© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Details
- Language :
- English
- ISSN :
- 1521-3773
- Volume :
- 63
- Issue :
- 17
- Database :
- MEDLINE
- Journal :
- Angewandte Chemie (International ed. in English)
- Publication Type :
- Academic Journal
- Accession number :
- 38506603
- Full Text :
- https://doi.org/10.1002/anie.202319158